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There is no easy answer to this issue. I have tried to come up withz a sustainable system to keep a repertoire current. Many true performers who play for a living have the same problem. But with all this North Star analysis and some contemplation on Comparative Thinking one has to ask himself why do you care? How many songs do you need in a playlist. Perhaps you could try building a playlist each quarter by season. There is Christmas, St. Patty’s, Spring Buegrass, Summer Blues, Fall Folk. You can change it up each years cycle. Truthfully, no one really want to hear us play for hours on end. Even at a Bluegrass or Folk jam 10 songs will be more than enough. TAC can cycle through 4 benchmark songs. Norwegian Wood, Sweet Home Chicago, I Can See Clearly Now, Folsom Prison Blues, Landslide, Friend of the Devil. That’s a good start.